Penna Holidays

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Penna Holiday

Our pick of the best Penna Hotel Deals

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
The price is NZ$1,005 per night from 10 Aug to 11 Aug
NZ$1,005
10 Aug - 11 Aug
includes taxes & fees
9.4/10 Exceptional! (219 reviews)
"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming ..."

Reviewed on 5 Aug 2026

Borgo Scopeto Wine & Country Relais
La Certosa di Pontignano

La Certosa di Pontignano

loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
The price is NZ$187 per night from 22 Aug to 23 Aug
NZ$187
22 Aug - 23 Aug
includes taxes & fees
9.4/10 Exceptional! (554 reviews)
"Great property with unique setting being an old monastery. We thought we had booked a room with A/C but there wasn’t. They moved us to a room with A/C at no additional cost."

Reviewed on 4 Aug 2026

La Certosa di Pontignano
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13 Gaiole in Chianti SI
The price is NZ$760 per night from 16 Aug to 17 Aug
NZ$760
16 Aug - 17 Aug
includes taxes & fees
9.6/10 Exceptional! (281 reviews)
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"

Reviewed on 4 Aug 2026

Castello di Spaltenna- Small Luxury Hotels of the World
See all 4,549 properties in Penna
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

What to do in Penna

Wine Experience In Chianti Hills & Radda In Chianti

Wine Tasting and Cellar Tour in the Heart of Tuscany from Florence

NZ$75
per adult
Wine Tasting and Cellar Tour in the Heart of Tuscany from Florence
Tour of the cellar and tasting of 6 wines

Tour of the cellar and tasting of 6 wines

NZ$59
per adult
Tour of the cellar and tasting of 6 wines
Arezzo: Val di Chiana Wine Tasting Experience

Arezzo: Val di Chiana Wine Tasting Experience

NZ$79
per adult
Arezzo: Val di Chiana Wine Tasting Experience
See all activities in Penna

Frequently asked questions

How much does a Penna holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Penna costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Penna?
January, February and March are the best times to look for cheap Penna holiday packages. Choosing to travel in quieter months means you can generally find better prices on hotels and flights.
How many days is enough for Penna?
The ideal duration for your Penna holiday depends on what you'd like to do and see. Generally, a handful of days to a week will give you plenty of time to visit all the leading attractions and discover some hidden spots along the way.
How to find the best Penna package deals?
Finding a cheap Penna package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply some filters and see what's available. You can customise your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most economical Penna package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Penna holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still have the freedom to create a personalised Penna holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Penna?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Penna adventure.
How to plan a trip to Penna?

  1. Choose when to get away: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to visit Penna.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to flights and experiences. Your accommodation will probably be the biggest expense during your trip to Penna.
  3. Decide how long to go for: Now that you're more familiar with Penna, you can figure out the ideal length of your holiday. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Penna holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.